Aluminium lithium hydride → HCID 11554303, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[5-tert-butyl-2-(4-cyano-phenyl)-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]urea (4.0 g, 8.8 mmol) in anhydrous THF (20 mL) was added a solution of lithium aluminum hydride in THF (1M, 9.7 mL, 9.7 mmol) with stirring at 0° C. under nitrogen, and then the reaction mixture was stirred at room temperature for 5 h. The excess lithium aluminum hydride was quenched by dropwise addition of EtOAc (5 mL) followed by EtOH (5 mL) and then 10% aqueous KHSO4 solution (5 mL). The reaction mixture was stirred at room temperature for an additional 10 min, and was then filtered through a pad of Celite® filter agent. The Celite® was washed with EtOH (50 mL) and the filtrate was concentrated at reduced pressure. The residue was purified by MPLC (80:20 CH2Cl2/MeOH) to give 3.2 g (79%) of the desired product. 1H-NMR (DMSO-d6) δ 9.38 (s, 1H), 8.41 (dd, J=1.5, 4.8 Hz, 2H), 7.49 to 7.46 (m, 6H), 7.07 (d, J=6.9 Hz, 2H), 6.85 (dd, J=1.8, 4.8 Hz, 2H), 6.32 (s, 1H), 3.82 (s, 2H), 1.26 (s, 9H); MS LC-MS [M+H]+=457, RT=1.96 min.

Provenance & Evidence